CN108504349B - Preparation method of rhodamine hybrid carbon dots and application of rhodamine hybrid carbon dots in mitochondrial targeting recognition - Google Patents
Preparation method of rhodamine hybrid carbon dots and application of rhodamine hybrid carbon dots in mitochondrial targeting recognition Download PDFInfo
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Abstract
The invention relates to a preparation method of rhodamine hybrid carbon dots and application thereof in mitochondrial targeting identification. According to the method, a microwave-assisted method is utilized, citric acid and m-aminophenol compounds are used as raw materials, the fluorescence emission wavelength can be effectively regulated and controlled by changing the form of meta-amino of phenol, rhodamine molecular fluorophore hybrid carbon dots are generated, and the preparation of controllable and predictable fluorescence emission wavelength carbon dots is realized. The method is simple to operate, raw materials are easy to obtain, and the method is green and environment-friendly, and creates a new strategy for synthesizing molecular fluorophore hybrid carbon dots. The carbon dots prepared by the method can be used for mitochondrial targeting identification in cells and have potential application values in the fields of biology, medical treatment and the like.
Description
Technical Field
The invention relates to the field of nano material manufacturing, in particular to a method for preparing rhodamine hybrid carbon dots by using a microwave-assisted method and a method for carrying out intracellular mitochondrial targeted identification by applying a nano material.
Background
After the development of a decade, Carbon Dots (CDs) as a novel photoluminescence nano material have been widely applied to the aspects of biomarkers, cancer diagnosis, fluorescence sensing, solar cells and the like due to the unique photoelectric properties of the CDs. Compared with the traditional semiconductor quantum dots (CdTe, CdSe and PbS), the carbon dots have the advantages of low toxicity, environmental friendliness, strong light stability, simple preparation method and the like, become research hotspots in the field of biological markers, and are considered as the most ideal fluorescent marker and detection material.
In the carbon dot "bottom-up" synthesis method, the selection of precursor molecules is particularly important, which determine the properties and application conditions of a synthesized target carbon dot to a certain extent, at present, a series of carbon dots with good fluorescence properties are synthesized by using common organic small molecules including citric acid, saccharides and amines as carbon sources through hydrothermal, microwave, ultrasonic, plasma treatment and the like (see: Zhu, s. j.; Meng, q. n.; Wang, L.; Zhang, j. h.; Song, y.b.; Jin, h.; Zhang, k.; Sun, h. C.; Wang, h. y.; Yang, b. angelm. int.ed., 2013, 52, 392012; Pan, L, L.; Sun, s.; Zhang, a. d.; Jiang, k. ang, n, h. C.; h.; h. C. h. n., 2013, 2012, p, L, p, n, L, g, n, p, n.
The rhodamine dye has wide application in the aspects of fluorescent labels, fluorescent probes and the like due to the advantages of large molar extinction coefficient, high fluorescence quantum yield, strong light stability and the like. The rhodamine fluorophore is hybridized into the interior or the surface of the carbon dot, and the rhodamine hybridization carbon dot (Rho-CDs) with high yield and specific recognition property can be controllably obtained.
Mitochondria serve as energy providers for cell life activities, and disorder thereof is related to various diseases of human, such as cardiovascular disease, Parkinson's disease, malignant tumor, and the like. Rhodamine molecules with positive charges tend to concentrate into mitochondria. Therefore, Rho-CDs also have the function of enriching in mitochondria, thereby realizing the imaging of mitochondria in cells.
Disclosure of Invention
The invention provides a method for preparing rhodamine molecular fluorophore hybrid carbon dots, which is simple to operate, easily available in raw materials and environment-friendly. The invention also relates to application of the carbon dots, namely application of the carbon dots in mitochondrial targeting identification in cells.
The technical scheme for realizing the invention is as follows: a preparation method of rhodamine hybrid carbon dots comprises the following steps:
(1) mixing citric acid and m-aminophenol compound, dissolving in distilled water to prepare precursor solution, and placing in a microwave reaction tube;
(2) placing the microwave reaction tube in the step (1) in a microwave reactor, heating the precursor solution to the temperature of 120 ℃ and 160 ℃, reacting for 0.5-6 h, and naturally cooling the obtained product to the room temperature;
(3) treating the product cooled in the step (2) by using a 0.22-micron filter membrane to remove large particles; then, treating the Rho-CDs by using an ultrafiltration tube with the interception amount of 3KDa to obtain a purified Rho-CDs solution;
(4) and (4) carrying out vacuum freeze drying on the Rho-CDs solution obtained in the step (3) to obtain Rho-CDs solid powder.
The intermediate aminophenol compound in the step (1) is any one of m-aminophenol, m-ethylamino-p-cresol, m-diethylaminophenol and 8-hydroxy julolidine.
The molar ratio of the citric acid to the m-aminophenol compound in the step (1) is (1: 2) - (2: 1).
The application steps of the rhodamine hybrid carbon dot in the mitochondrial targeting recognition are as follows:
(1) cells were seeded in a confocal dish at 37 ℃ with 5% CO2Culturing in a cell culture box with saturated humidity for 12-24 h to obtain a culture solution A;
(2) adding Rho-CDs into the culture solution A obtained in the step (1), and adding 5% CO at 37 DEG C2Culturing for 4 h in a cell culture box with saturated humidity to obtain a culture solution B;
(3) adding a mitochondrial coloring agent Rho123 into the culture solution B obtained in the step (2), and incubating for 10 min to obtain a culture solution C;
(4) staining reagent NucRedTML ive 647, adding into the culture solution C obtained in the step (3), and incubating for 10 min to obtain a mixed solution D;
(5) washing the cells with phosphate buffer, and then adding fresh phenol red-free cell culture fluid; and (4) shooting and imaging by using a laser confocal microscope.
The cell in the step (1) is any one of Hela cell, A549 cell, MCF7 cell and 3T3 cell.
And (2) the cell culture solution in the confocal dish in the step (1) consists of a DMEM high-sugar medium, 10 volume percent of fetal bovine serum, 100 mu g/m L penicillin and 100 mu g/m L streptomycin.
The concentration of Rho-CDs added in step (2) is 50 μ g/m L.
The concentration of the mitochondrial stain Rho123 added in the step (3) is 1 μ M.
The nuclear staining reagent NucRed in the step (5)TML ive 647 the concentration of the solution after addition was 2 drops/m L.
The invention has the beneficial effects that: the method utilizes a microwave-assisted method, takes common citric acid and m-aminophenol substances as raw materials, effectively regulates and controls the fluorescence emission wavelength by changing the form of meta-amino of phenol, successfully generates and hybridizes a rhodamine molecular fluorophore into a carbon dot, and realizes the preparation of the controllable and predictable fluorescence emission wavelength carbon dot. The Rho-CDs have excellent fluorescence, simple preparation and environmental protection. Meanwhile, the carbon dots can carry out targeted recognition on cell mitochondria and have value in further application to research on related diseases of the mitochondria.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic diagram of rhodamine hybrid carbon dots (Rho-CDs) and a fluorescence photograph of the rhodamine hybrid carbon dots.
FIG. 2 is a UV absorption spectrum of Rho-CDs 580, Rho-CDs 520, Rho-CDs 540 and Rho-CDs600 prepared in examples 1, 2, 3 and 4.
FIG. 3 is a chart of the excitation spectra of Rho-CDs 580, Rho-CDs 520, Rho-CDs 540 and Rho-CDs600 prepared in examples 1, 2, 3 and 4.
FIG. 4 is a fluorescence emission spectrum of Rho-CDs 580, Rho-CDs 520, Rho-CDs 540 and Rho-CDs600 prepared in examples 1, 2, 3 and 4.
FIG. 5 is a transmission electron micrograph of Rho-CDs 580 prepared according to example 1.
FIG. 6 is a graph showing the distribution of the carbon dot particle size of Rho-CDs 580 prepared in example 1.
FIG. 7 shows the fluorescence emission spectra of carbon dots of Rho-CDs 580 prepared in example 1 at different excitation wavelengths (excitation wavelengths 470nm, 480 nm, 490 nm, 500 nm, 510 nm, 520 nm, 530 nm, 540 nm, 550 nm).
FIG. 8 application of Rho-CDs 580 prepared in example 1 in mitochondrial targeting recognition in cells, Rho123 and NucRedTML ive 6470 staining pattern and overlay.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
Example 1
A preparation method of Rho-CDs 580, comprising the following steps:
mixing 30 mg of citric acid and 12.9 mg of m-diethylaminophenol (molar ratio =2: 1) and dissolving in 2 m L of distilled water to prepare a precursor solution, placing the precursor solution in a microwave reaction tube, placing the microwave reaction tube in a microwave reactor, heating the precursor solution to 160 ℃, reacting for 2 h, naturally cooling the obtained product to room temperature, treating with a 0.22 mu m filter membrane to remove large particles, treating with an ultrafiltration tube with a cut-off of 3KDa to remove unreacted raw materials to obtain a purified Rho-CDs 580 solution, carrying out vacuum freeze drying on the Rho-CDs 580 solution to obtain Rho-CDs 580 solid powder, wherein the ultraviolet-visible light absorption spectrum, the excitation spectrum and the fluorescence emission spectrum of the Rho-CDs 580 solution are shown in figures 2-4, the electron microscope diagrams and the particle size distribution diagrams of the Rho-CDs 580 are shown in figures 5 and 6, the fluorescence emission diagrams under different excitations are shown in figure 7, the curve of figure 7 corresponds to the label from bottom, namely 470nm corresponds to the lowest curve, and the rest is analogies.
Example 2
The preparation method of Rho-CDs 520 comprises the following steps:
30 mg of citric acid and 8.5 mg of m-aminophenol (molar ratio =2: 1) were mixed and dissolved in 2 m L of distilled water to prepare a precursor solution, the rest of the steps were as in example 1. the ultraviolet-visible light absorption spectrum, excitation spectrum and fluorescence emission spectrum of the Rho-CDs 520 solution are shown in FIGS. 2-4.
Example 3
The preparation method of Rho-CDs 540 comprises the following steps:
30 mg of citric acid and 11.8 mg of m-ethylamino-p-cresol (molar ratio =2: 1) were mixed and dissolved in 2 m L of distilled water to prepare a precursor solution, and the rest of the steps were as in example 1. the ultraviolet-visible absorption spectrum, excitation spectrum and fluorescence emission spectrum of Rho-CDs 540 solution are shown in FIGS. 2 to 4.
Example 4
The preparation method of Rho-CDs600 comprises the following steps:
30 mg of citric acid was mixed with 14.8 mg of 8-hydroxycitropin (molar ratio =2: 1) and dissolved in 2 m L of distilled water to prepare a precursor solution, and the rest of the steps were as in example 1. the ultraviolet-visible absorption spectrum, excitation spectrum and fluorescence emission spectrum of Rho-CDs600 solution are shown in FIGS. 2-4.
Example 5
A preparation method of Rho-CDs 580, comprising the following steps:
mixing 7.5 mg of citric acid and 12.9 mg of m-diethylaminophenol (molar ratio =1: 2) and dissolving in 2 m L of distilled water to prepare a precursor solution, placing the precursor solution in a microwave reaction tube, placing the microwave reaction tube in a microwave reactor, heating the precursor solution to 120 ℃, reacting for 6 hours, naturally cooling the obtained product to room temperature, treating the product with a 0.22 mu m filter membrane to remove large particles, treating the product with an ultrafiltration tube with a cutoff of 3KDa to remove unreacted raw materials to obtain a purified Rho-CDs 580 solution, and carrying out vacuum freeze drying on the Rho-CDs 580 solution to obtain Rho-CDs 580 solid powder.
Example 6
A preparation method of Rho-CDs 580, comprising the following steps:
mixing 15 mg of citric acid and 12.9 mg of m-diethylaminophenol (molar ratio =1: 1) and dissolving the mixture in 2 m L of distilled water to prepare a precursor solution, placing the precursor solution in a microwave reaction tube, placing the microwave reaction tube in a microwave reactor, heating the precursor solution to 140 ℃, reacting for 0.5 h, naturally cooling the obtained product to room temperature, treating the product with a 0.22 mu m filter membrane to remove large particles, treating the product with an ultrafiltration tube with a cutoff of 3KDa to remove unreacted raw materials to obtain a purified Rho-CDs 580 solution, and carrying out vacuum freeze drying on the Rho-CDs 580 solution to obtain Rho-CDs 580 solid powder.
The method is applied to targeted recognition of mitochondria in cells and comprises the following steps:
hela cells were seeded in a confocal dish at 37 ℃ with 5% CO2Culturing in a cell culture box with saturated humidity for 24 h (cell culture)The nutrient solution comprises DMEM high-sugar medium, 10% volume percent of fetal calf serum, 100 mu g/m L penicillin and 100 mu g/m L streptomycin, Rho-CDs 580 is prepared into solution and added into a confocal dish to ensure that the final concentration is 50 mu g/m L, and 5% CO is added at 37 DEG C2Culturing for 4 h in a cell culture box with saturated humidity; in order to examine the accuracy of Rho-CDs 580 on the mitochondrial targeting recognition function, a commercial mitochondrial stain Rho123 was added into a confocal culture dish at a final concentration of 1 μ M and incubated for 10 min; and staining the nucleus with the reagent NucRedTML ive 647 is added into a confocal dish for 2 d/m L to incubate for 10 min, the mixed solution is removed, phosphate buffer solution is used for washing cells for 3 times, fresh DMEM high-glucose cell culture solution without phenol red is added, a laser confocal microscope is used for shooting and imaging, a laser with the wavelength of 552 nm is used for irradiating, a fluorescence image in the range of 560-650 nm is collected and corresponds to a Rho-CDs 580 staining area, a laser with the wavelength of 488 nm is used for collecting a fluorescence image in the range of 500-550nm and corresponds to a commercialized mitochondrial staining area Rho123, a laser with the wavelength of 638 nm is used for collecting a fluorescence image in the range of 650-750 nm and corresponds to a nuclear staining reagent NucRedTML ive 6470 stained areas the picture of the results is shown in figure 8.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (8)
1. A preparation method of rhodamine hybrid carbon dots is characterized by comprising the following steps:
(1) mixing citric acid and m-aminophenol compound, dissolving in distilled water to prepare precursor solution, and placing in a microwave reaction tube; the m-aminophenol compound is any one of m-aminophenol, m-ethylamino p-cresol, m-diethylaminophenol and 8-hydroxy julolidine;
(2) placing the microwave reaction tube in the step (1) in a microwave reactor, heating the precursor solution to 160 ℃ at 120 ℃, reacting for 0.5-6 h, and naturally cooling the product after reaction to room temperature;
(3) treating the product cooled in the step (2) by using a 0.22-micron filter membrane to remove large particles; treating with ultrafiltration tube with cut-off of 3KDa to obtain purified Rho-CDs solution;
(4) and (4) carrying out vacuum freeze drying on the Rho-CDs solution obtained in the step (3) to obtain Rho-CDs solid powder.
2. The method for preparing rhodamine hybrid carbon dots according to claim 1, wherein the method comprises the following steps: the molar ratio of the citric acid to the m-aminophenol compound in the step (1) is (1: 2) - (2: 1).
3. The application of the rhodamine hybrid carbon dot as described in any one of claims 1-2 in preparing a mitochondrial targeting recognition detection reagent is characterized by comprising the following steps:
(1) cells were seeded in a confocal dish at 37 ℃ with 5% CO2Culturing in a cell culture box with saturated humidity for 12-24 h to obtain a culture solution A;
(2) adding Rho-CDs into the culture solution A obtained in the step (1), and adding 5% CO at 37 DEG C2Culturing for 4 h in a cell culture box with saturated humidity to obtain a culture solution B;
(3) adding a mitochondrial coloring agent Rho123 into the culture solution B obtained in the step (2), and incubating for 10 min to obtain a culture solution C;
(4) staining reagent NucRedTML ive 647, adding into the culture solution C obtained in the step (3), and incubating for 10 min to obtain a mixed solution D;
(5) washing the cells with phosphate buffer, and then adding fresh phenol red-free cell culture fluid; and (4) shooting and imaging by using a laser confocal microscope.
4. The application of the rhodamine hybrid carbon dot in preparing a mitochondrial targeting recognition detection reagent according to claim 3, wherein the rhodamine hybrid carbon dot is characterized in that: the cell in the step (1) is any one of Hela cell, A549 cell, MCF7 cell and 3T3 cell.
5. The application of the rhodamine hybrid carbon dot in preparing the mitochondrial targeting recognition detection reagent as claimed in claim 3, wherein the cell culture solution in the confocal dish in the step (1) consists of a DMEM high-sugar medium, 10 volume percent of fetal bovine serum, 100 μ g/m L penicillin and 100 μ g/m L streptomycin.
6. The application of the rhodamine hybrid carbon dot in preparing the mitochondrial targeting recognition detection reagent according to claim 3, wherein the concentration of the Rho-CDs added in the step (2) is 50 μ g/m L.
7. The application of the rhodamine hybrid carbon dot in preparing a mitochondrial targeting recognition detection reagent according to claim 3, wherein the rhodamine hybrid carbon dot is characterized in that: the concentration of the mitochondrial stain Rho123 added in the step (3) is 1 μ M.
8. The application of the rhodamine hybrid carbon dot in preparing a mitochondrial targeting recognition detection reagent according to claim 3, wherein the rhodamine hybrid carbon dot is characterized in that: the nuclear staining reagent NucRed in the step (4)TML ive 647 the concentration of the solution after addition was 2 drops/m L.
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| CN110040717B (en) * | 2019-06-03 | 2020-11-06 | 四川中科微纳科技有限公司 | Method for preparing high-purity multicolor carbon dots by regulating and controlling carbon nanocrystalline morphology and application |
| CN110982513B (en) * | 2019-11-29 | 2022-10-04 | 郑州大学 | Preparation method of fluorescent carbon dots and application of fluorescent carbon dots in cell imaging |
| CN113548656B (en) * | 2020-06-16 | 2023-02-21 | 哈尔滨成程生命与物质研究所 | Carbon dots with anticancer bioactivity and preparation method thereof |
| CN113698928A (en) * | 2021-09-02 | 2021-11-26 | 深圳大学 | Carbon dot, preparation method thereof and application of carbon dot in preparation of mitochondrial-targeted fluorescent probe |
| CN114350357B (en) * | 2022-01-11 | 2023-07-25 | 郑州大学 | Preparation and application of fluorescent carbon dot capable of circularly and rapidly detecting malachite green |
| CN117106447A (en) * | 2023-05-18 | 2023-11-24 | 安徽师范大学 | Mitochondria targeted fluorescent carbon dot and preparation method and application thereof |
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